Related Experiment Video
Updated: Apr 21, 2026
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Synthesis, Photophysical, and Chiroptical Properties of Optically Active BINOL-Boranil Enantiomers
Samuel Decorps1, Rayan Hachem1, Juichi Bainvel-Sato1
1ENS de Lyon, CNRS, LCH, UMR 5182, 69342, Lyon Cedex 07, France.
None:
We describe a very simple and efficient gram-scale synthetic pathway toward Boranils substituted directly on the boron center by 1,1'-bi-2-naphthol derivatives (BINOL). Properties of the resulting BINOL-Boranils were investigated by nuclear magnetic resonance (NMR), UV-visible, fluorescence, electronic circular dichroism (ECD), and circularly polarized luminescence (CPL) spectroscopies. Insight into the molecular structure is also provided based on single-crystal X-ray diffraction experiments. These chiral dyes typically feature high molar absorption coefficients in the range of 35,000 to 90,000 M-1·cm-1, absorption dissymmetry factors (g abs) in the range of 2.5-5.5 × 10-4 at the maximum wavelength of absorption of Boranils, and CPL brightness up to B CPL = 5.4 M-1·cm-1.
Related Concept Videos
02:24Properties of Enantiomers and Optical Activity
02:05Prochirality
02:52Stereoisomerism
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
00:58¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
01:12Stereochemical Effects of Enolization